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<h1><a href="https://archiveofourown.org/works/25350844">Deeper Feelings</a> by <a class='authorlink' href='https://archiveofourown.org/users/meaningfulbliss/pseuds/meaningfulbliss'>meaningfulbliss</a></h1>

<table class="full">

<tr><td><b>Category:</b></td><td>Supernatural</td></tr>

<tr><td><b>Genre:</b></td><td>Explicit Language, F/M, Originally Posted on Tumblr</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>In-Progress</td></tr>

<tr><td><b>Published:</b></td><td>2020-07-18</td></tr>

<tr><td><b>Updated:</b></td><td>2020-07-18</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-05 07:15:02</td></tr>

<tr><td><b>Rating:</b></td><td>Not Rated</td></tr>

<tr><td><b>Warnings:</b></td><td>No Archive Warnings Apply</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>2,407</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/25350844</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/meaningfulbliss/pseuds/meaningfulbliss</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>Keegan has always had a crush on her best friend’s dad, Sam Winchester. As graduation grows closer and she starts spending more and more time with him, alone and with her friend, the crush begins to turn into much deeper feelings.</p><p>Sam never realized how much of an amazing woman his daughter was friends with. At first he just thought that she was like a daughter to him but that soon changes.</p><p>Because of the time spent together their feelings grow deeper for each other and become mutual. The only problem is whether they should act on the feelings they have or keep them to themselves.</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Sam Winchester/Original Female Character(s)</td></tr>

<tr><td><b>Comments:</b></td><td>2</td></tr>

<tr><td><b>Kudos:</b></td><td>2</td></tr>

</table>

<a name="section0001"><h2>Deeper Feelings</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Summary for the Chapter:</b><blockquote class="userstuff">
            <p>Keegan is having dinner with Brook and Sam Winchester when she gets offered a job by Sam. Unbeknownst to her best friend, Brook, and her best friend’s dad, Sam, she has a major crush on Sam Winchester. Sam feels nervous being around Keegan and can’t figure out why, she’s just his daughter’s best friend.</p>
          </blockquote></div><div class="userstuff module">
    
    <p>
  <strong>✰Keegan's POV✰</strong>
</p><p>I stared at my reflection in the mirror, admiring the dress that I had picked up for graduation earlier while shopping with my best friend. The ruffles along my shoulders and at the bottom near the middle of my thighs were adorable, the fabric was soft to the touch, and the dress hugged my curves perfectly. In the mirror I could see Brook, my best friend, walking up behind me. She looked at me in the dress and said, “Kee, you could not have picked a better dress for yourself. It fits you perfectly and looks absolutely amazing on you! You could steal anyone’s heart wearing that dress!”</p><p>Brook and I have shared an apartment for the past three years that we have been in college. Freshman year we were roommates in the dorms and instantly clicked as friends, by the end of the year we agreed to split the rent on an apartment and it was the utmost best decision we ever could have made. Now we’re seniors with two weeks left before graduation and inseparable. </p><p>“Don’t get me wrong Kee, I love seeing you in that dress but we need to get ready. My dad is meeting us at the restaurant in an hour.”<br/>
“Shit! B! You couldn’t have told me sooner?! I still need to shower, dry my hair, and get dressed! Ughhh I hate when I’m running behind.”<br/>
“You have time, jeez, it’s not like you have to dress to impress, it's only us and my dad going. Chloe told me she has to go to dinner with her sisters so I’m a lone woman tonight alongside my bestie.”</p><p>Not known to Brook, I have to dress at least half decent because of the fact that Brook’s father, Sam Winchester, is the hottest and sweetest man to ever walk the earth. No matter how many times he has seen me dressed in sweatpants and a baggy t-shirt with a messy bun on top of my head, if I have the chance to dress in a way that he might find to be attractive I will. </p><p>Pulling off the dress and hanging it against the body-length mirror near my desk, I headed to the bathroom connected to my room to take a shower. Grabbing a towel from a shelf in the bathroom I placed it on the vanity before turning on the water to the shower. Stripping my bra and panties, I stepped into the shower feeling the hot water brush off the nervousness of sitting at the dinner table with Sam and Brook for around an hour. </p><p>After washing up, I stepped out of the shower wrapping the towel I had grabbed before around my body and walking to my closet to pick out an outfit for dinner. Looking at my clothes I decided on a pair of high-waisted white skinny jeans with a hole in each knee, a simple flowy black spaghetti strapped shirt, and a pair of black booties. Grabbing my black push up bra and matching thong I put them on before pulling my jeans up my legs and my shirt over my head. Walking back into the bathroom, I put on a little mascara and swiped some clear lip gloss and kept it as I walked over to my desk putting it in my purse. Putting my purse on my shoulder, I slid on my jean jacket that was hanging on the back of my desk chair and walked out of my room to meet Brook. </p><p>“Are you driving?” Brook asked as she locked the door to our apartment and we headed down the stairs to the parking lot.<br/>
“Don’t I always?” I laughed and pulled my keys out of my purse just as we got to my jeep parked in the front of the parking lot.<br/>
Both of us laughed at the comment I made because of how true it is, we hopped into my jeep and I started asking her what restaurant we were meeting her dad at.<br/>
“The italian restaurant on the corner that we always go to,” she told me as I pulled out of my parking spot and headed to the exit of the lot. </p><p>Pulling out onto the main road, Brook turned the music on the radio up loud and we both sang our hearts out for the quick ten minute drive to the restaurant. Getting into the parking lot I found a parking spot easily in the front since it was only a Wednesday. Turning off my jeep and both of us getting out grabbing our purses, I locked it and we made our way to the front doors of the restaurant. </p><p>When we walked in the front door Brook immediately saw her dad sitting at a booth in the back. As we walked up to the booth he looked up and saw each of us, getting up to greet us both he hugged Brook tightly first. I slightly looked over every square inch of him. He was wearing a nice pair of dark blue jeans that made his legs look longer if that was even possible, the black shirt he had on was just tight enough to show off his muscular chest, and the flannel he wore over his shirt was rolled up to his elbows and showed off his fantastic arms. Not to mention his long, brown hair looked soft enough that I just wanted to run my fingers through it and the scruff on his jawline like he hadn’t shaved in a couple days was beyond sexy. God how was this man in his forties?</p><p>After Sam finished hugging Brook, I walked up and gave him a hug. Pulling away slightly from the hug, Sam looked at me with a smile, “Keegan, you look just as gorgeous as always,” his hand lingering on the small of my back as I sat in the booth next to Brook, followed by Sam sitting on his side across from us. My mind couldn’t get over the way he kept his hand on my back for so long but I just chalked it up to me overthinking it. </p><p>After we ordered our drinks, Brook looked at me telling me that she needed the bathroom so I got up and let her out before sitting back down, alone at the table with Sam. Silently cursing myself for not going with Brook. </p><p>“So, Mr. Winchester, how are things going over at the bar?” I asked trying to make small talk until Brook got back.<br/>
“Keegan, how many times have I told you that you can call me Sam?” he chuckled and flashed a huge smile at me before continuing with his response. “Well you know my brother, Dean, has always been such a great help and it was such a great idea for us to go in as partners instead of alone, and he’s been helping out a lot with the bartending especially now since I’m getting prepared for you and Brook to be graduating,” he said as he rubbed the back of his neck, a nervous tick of his you had noticed over the past few years but it confused me as to why he was doing it while talking to me. “Um, Dean actually tells me that he sees you in there quite a bit, but somehow you manage to be there when I’m not.”<br/>
Letting out a nervous chuckle, I looked up at him through my eyelashes, “Yea, uh, I tend to go when I have a rough or long day, you know? And with graduation coming up it seems there’s been a lot of those lately. You might as well give me a job helping bartend. I have been there so often.”<br/>
“If you’re interested. It couldn’t hurt having such a pretty woman behind the bar,” he said, meeting my eyes. I gave him a soft smile but neither one of us pulled our eyes away from the other, I could swear I saw some time of emotion in his eye that I hadn’t seen before. </p><p>Hearing Brook’s voice as she came back to the table, both me and Sam looked away from each other before I got out of the booth to let Brook back in. As the waiter came back with our drinks we all ordered our food and started to talk about what Brook and I had left for our classes. </p><p>“I know Brook only has one final left on Friday, do you have anything left to do Keegan?” Sam asked me after taking a sip of his water.<br/>
“Well, actually, no. I took my last final on Monday so I have absolutely nothing to do until graduation,” I told him and took a sip of my sweet tea.<br/>
“You could start training on Friday if you’d like. I wasn’t joking about you coming bartend. Plus you’d start getting free drinks instead of having to pay every time you came,” he told me with a laugh.<br/>
Brook looked at both of us with this quizzical expression on her face, completely confused about what we were talking about. </p><p>Looking to Brook I gave her a smile, “Your dad offered me a job bartending at the bar,” I told her to clear up her confusion.<br/>
“Ohh, that sounds like a great idea, are you going to take it Kee?” she asked me.<br/>
Biting my lip and looking between her and Sam, I let out a nervous laugh, “Sure, I don’t see why not,” and I instantly regretted my statement because that would mean I’d be spending a whole lot more time with Sam without Brook being there. </p><p>Finishing our meals, we were all completely full and ready to go home. The waiter came by with the check and Sam automatically gave him his card. Brook looked at him with a glare, “Dad, you don’t have to do that, we can pay for ourselves.” After Sam took the last sip of his water, he looked between me and Brook, “I know, but consider it my treat. I don’t get to see you two women as often as I’d like,” and with his last few  words his eyes landed on me. Those words instantly made me blush and I had to look down so that he wouldn’t notice. </p><p>When the waiter got back with Sam’s card and the receipt we all got up and made our way to the doors. After Brook gave her dad a hug goodbye, Sam looked at me and asked if I could stay and talk to him about Friday. “Oh, uh, yeah of course,” I responded when he asked, giving the keys to Brook I said with a laugh, “You can start it. Just do not go anywhere because that gives you the ability to wreck it!” </p><p>Turning back to Sam, “So what about Friday did you want to talk about?” I asked him.<br/>
“I genuinely am offering you a job if you don’t think I am,” he started with a chuckle and started rubbing to back of his neck nervously for some unknown reason, “and, uh, I’m going to personally train you on Friday so that you don’t have to worry about it being Dean, someone that you don’t know all that well,” he explained to me.<br/>
“I actually was a bartender for a few months freshman year so it’s fine if Dean trains me, I’m sure I’ll get the hang of it pretty quickly,” I assured him, desperately trying to not have to spend an entire first night working with him.<br/>
“Keegan, I insist. Plus, it’ll give me some time to get to know you more because I don’t know really all too much about you,” he said with what looked to be a nervous smile on his face.<br/>
“Okay, I guess if you insist. I’ll see you Friday, I have to go before Brook messes anything up in my jeep,” I said with a laugh, “you know how that is.”<br/>
“Yep I sure do,” he laughed. Giving me a hug goodbye I again felt as if his hand lingered on my lower back but it was probably nothing.<br/>
Walking to my jeep I put my head in my hands out of nervous habit over actually agreeing to take a job at Sam’s bar and to be trained by him. Yet, I smiled when I lifted my head back up because I was kind of happy to spend alone time with him and that he wanted to get to know me more, even if it was just because I’m his daughter's best friend. </p><p>
  <strong>✰Sam's POV✰</strong>
</p><p>Running my hands down my face I let out a huge sigh, not out of relief but out of nervousness surprisingly. I had been nervous throughout the whole dinner and I couldn’t even start to understand why. </p><p>Keegan is Brook’s best friend, I’ve known her for four years, but yet somehow she surprises me. She always looked amazing, but tonight for some unknown reason her looks really hit me. The way her dark hair flowed over her shoulders, the way her shirt had dipped just low enough to show off a little cleavage, and the way her jeans perfectly shaped her hips and ass. And damn, the ass that woman had. But god, there was no reason for me to be thinking about her in that way, she was basically a daughter to me, right? Then I had to go and offer her a job, where she would wear clothes a lot more revealing than what she wore tonight. </p><p>Throwing my head back against the seat I kept thinking about how I couldn’t even talk to her without getting nervous. Not even because of how she looks but because of how sweet her voice sounded and how cute she was when she was laughing. </p><p>What was going on in my pants? Sure it had been way too long since I’d been with someone else but that didn’t mean I was becoming attracted to Keegan that way because of it. And more importantly what was going on with my heart and why was I feeling this way all of a sudden? </p><p>I would really have to get it together before I spent the whole night with her on Friday. Putting the key in the ignition of my car I turned it on and quickly pulled out hoping that occupying myself with driving would take my mind off of her.</p>
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